Acetoacetic acid

3-oxobutanoic acid, diacetic acid

Identifiers
CAS
number
541-50-4

PubChem 96
ChemSpider
94

DrugBank DB01762
KEGG
C00164

ChEBI
CHEBI:15344

ChEMBL
CHEMBL1230762

Jmol-3D
images
Image 1
(http://chemapps.stolaf.edu/jmol/jmol.php?
model=O%3DC%28C%29CC%28%3DO%29O)
Properties
Molecular
formula
C
4
H
6
O
3
Molar mass 102.088 g/mol
Appearance colorless, oily liquid
Melting
point
36.5 C (97.7 F; 309.6 K)
Acetoacetic acid
From Wikipedia, the free encyclopedia
Acetoacetic acid (also called diacetic acid) is the
organic compound with the formula
CH
3
COCH
2
COOH. It is the simplest beta-keto acid
group and like other members of this class is unstable.
The methyl and ethyl esters, which are quite stable,
are produced on a large scale industrially as
precursors to dyes.
[2]
Contents
1 Synthesis and properties
2 Applications
3 Detection
4 See also
5 References
Synthesis and properties
In general, the esters are prepared from diketene by
treatment with alcohols.
[2]
Acetoacetic acid can be
prepared by the hydrolysis of the ethyl acetoacetate
followed by acidification of the anion.
[3]
In general,
acetoacetic acid is generated at 0 C and used in situ
immediately.
[4]
It decomposes at a moderate rate to
acetone and carbon dioxide:
CH
3
C(O)CH
2
CO
2
H CH
3
C(O)CH
3
+
CO
2
The acid form has a half-life of 140 minutes at 37 C
in water, whereas the basic form (the anion) has a
half-life of 130 hours. That is, it reacts about 55 times
more slowly.
[5]
It is a weak acid (like most alkyl carboxylic acids)
with a pK
a
of 3.58.
IUPAC name
SMILES
InChI
Boiling
point
Decomposes
Solubility in
water
miscible
Solubility soluble in ethanol, ether
Acidity
(pK
a
)
3.58 [1]
Except where noted otherwise, data are given for materials in
their standard state (at 25 C (77 F), 100 kPa)
(verify) (what is: / ?)
Infobox references
Pigment Yellow 16 is a typical dye
containing the acetoacetyl group
Applications
Acetoacetic esters are used for the acetoacetylation
reaction, which is widely used in the production of
arylide yellows and diarylide dyes.
[2]
Although the
esters can be used in this reaction, diketene also
reacts with alcohols and amines to the corresponding
acetoacetic acid derivatives in a process called
acetoacetylation. An example is the reaction with 2-
aminoindane:
[6]
.
Detection
When ketone bodies are measured by way of urine concentration,
acetoacetic acid, along with beta-hydroxybutyric acid (BHB), and
acetone, is what is detected. This is done using dipsticks coated in
nitroprusside or similar reagents. Nitroprusside changes from pink to
purple in the presence of acetoacetate, the conjugate base of acetoacetic
acid, and the colour change is graded by eye. The popular dipstick used to detect ketone bodies in urine "Ketostix"
by Bayer, only detects acetoacetate, not BHB or acetone.
See also
3-hydroxybutyrate dehydrogenase
References
1. ^ Dawson, R. M. C., et al., Data for Biochemical Research, Oxford, Clarendon Press, 1959.
2. ^
a

b

c
Franz Dietrich Klingler, Wolfgang Ebertz "Oxocarboxylic Acids" in Ullmann's Encyclopedia of Industrial
Chemistry 2005, Wiley-VCH, Weinheim. doi:10.1002/14356007.a18 313
(http://dx.doi.org/10.1002%2F14356007.a18+313)
3. ^ Robert C. Krueger (1952). "Crystalline Acetoacetic Acid". Journal of the American Chemical Society 74 (21):
55365536. doi:10.1021/ja01141a521 (http://dx.doi.org/10.1021%2Fja01141a521).
4. ^ George A. Reynolds and J. A. VanAllan "Methylglyoxal--Phenylhydrazone" Organic Syntheses, Collected
Volume 4, p.633 (1963).http://www.orgsyn.org/orgsyn/pdfs/CV4P0633.pdf
5. ^ Hay, R. W.; Bond, M. A. (1967). "Kinetics of decarboxilation of acetoacetic acid". Aust. J. Chem. 20 (9): 1823
8. doi:10.1071/CH9671823 (http://dx.doi.org/10.1071%2FCH9671823).
6. ^ Kiran Kumar Solingapuram Sai, Thomas M. Gilbert, and Douglas A. Klumpp (2007). "Knorr Cyclizations and
Distonic Superelectrophiles". J. Org. Chem. 72 (25): 97619764. doi:10.1021/jo7013092
(http://dx.doi.org/10.1021%2Fjo7013092). PMID 17999519 (https://www.ncbi.nlm.nih.gov/pubmed/17999519).
Retrieved from "http://en.wikipedia.org/w/index.php?title=Acetoacetic_acid&oldid=599129056"
Categories: Ketones
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